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Chemistry

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Also known as: 591-64-0, Calcium 4-oxopentanoate, Calcium levulinate anhydrous, Calcium bis(4-oxovalerate), Pentanoic acid, 4-oxo-, calcium salt, Levulinic acid calcium salt
Molecular Formula
C10H14CaO6
Molecular Weight
270.29  g/mol
InChI Key
APKDPOQXVKRLEP-UHFFFAOYSA-L
FDA UNII
LLQ966USIL

Calcium Levulinate
The relatively new calcium levulinate is produced from a direct reaction between L- or levulinic acid levulose and calcium hydroxide. The resultant calcium levulinate formulation, when used as a calcium supplement, possesses a high calcium content that is observed to be 14.8% higher than the content typically found in calcium lactate. This formulation is considered a low molecular weight organic calcium ion type that is easily absorbed through the intestinal wall. This new application of calcium is intended for use as a food fortifier, to fortify foods like sauces, condiments, beer, beverages, soft drinks, milk and milk products, soy milk and soy products with calcium nutrition. Calcium levulinate can be used alone, or with calcium lactate, calcium chloride, and other compounds, either for pharmaceutical tablets, capsules, or injections preparation.
1 2D Structure

Calcium Levulinate

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
calcium;4-oxopentanoate
2.1.2 InChI
InChI=1S/2C5H8O3.Ca/c2*1-4(6)2-3-5(7)8;/h2*2-3H2,1H3,(H,7,8);/q;;+2/p-2
2.1.3 InChI Key
APKDPOQXVKRLEP-UHFFFAOYSA-L
2.1.4 Canonical SMILES
CC(=O)CCC(=O)[O-].CC(=O)CCC(=O)[O-].[Ca+2]
2.2 Other Identifiers
2.2.1 UNII
LLQ966USIL
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 4-oxopentanoic Acid, 4-ketovaleric Acid

2. Calcium Levulate

3. Diasporal

4. Gamma-ketovaleric Acid

5. Levulinic Acid

6. Levulinic Acid, Ammonium Salt

7. Levulinic Acid, Calcium Salt

8. Levulinic Acid, Sodium Salt

9. Magnesium Diasporal

10. Magnesium Laevulinate

11. Magnesium Levulinate

2.3.2 Depositor-Supplied Synonyms

1. 591-64-0

2. Calcium 4-oxopentanoate

3. Calcium Levulinate Anhydrous

4. Calcium Bis(4-oxovalerate)

5. Pentanoic Acid, 4-oxo-, Calcium Salt

6. Levulinic Acid Calcium Salt

7. Calcium;4-oxopentanoate

8. Calcium Laevulate

9. Calcium Levulinate Dihydrate

10. Llq966usil

11. Laevucalcin

12. Pentanoic Acid, 4-oxo-, Calcium Salt (2:1)

13. Flanthin

14. Levucal

15. Calcium Laevulinate

16. Levulin Calcid

17. Calcium Pharmacon

18. Calcium-diasporal

19. Mil-u-cal

20. Levulinic Acid, Calcium Salt

21. Einecs 209-725-9

22. Unii-llq966usil

23. Ai3-04042

24. Schembl116039

25. 4-oxovaleric Acid Calcium Salt

26. Calcium Levulinate [mi]

27. Calcium 4-oxidanylidenepentanoate

28. Dtxsid8060454

29. Calcium Levulinate (1:2)

30. 3-acetylpropionic Acid Calcium Salt

31. Calcium Laevulinate [who-dd]

32. Mfcd00045959

33. Akos015915020

34. Db13800

35. Db-053333

36. Cs-0187336

37. Ft-0632457

38. L0043

39. H10799

40. (2-ethyl-1h-benzimidazol-1-yl)aceticacid

41. A832191

42. Q27155578

2.4 Create Date
2005-08-08
3 Chemical and Physical Properties
Molecular Weight 270.29 g/mol
Molecular Formula C10H14CaO6
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count6
Rotatable Bond Count4
Exact Mass270.0416290 g/mol
Monoisotopic Mass270.0416290 g/mol
Topological Polar Surface Area114 Ų
Heavy Atom Count17
Formal Charge0
Complexity101
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count3
4 Drug and Medication Information
4.1 Drug Indication

This new application of calcium is intended for use as a food fortifier, to fortify foods like sauces, condiments, beer, beverages, soft drinks, milk and milk products, soy milk and soy products with calcium nutrition. Calcium levulinate can be used alone, or with calcium lactate, calcium chloride, and other compounds, either for pharmaceutical tablets, capsules, or injections preparation. In essence, calcium levulinate is ultimately a relatively new calcium supplementation option.


5 Pharmacology and Biochemistry
5.1 Pharmacology

The relatively new calcium levulinate is produced from a direct reaction between L- or levulinic acid levulose and calcium hydroxide. The resultant calcium levulinate formulation, when used as a calcium supplement, possesses a high calcium content that is observed to be 14.8% higher than the content typically found in calcium lactate. Moreover, this formulation also demonstrates a high solubility of more than 30% at 25. Furthermore, the calcium levulinate is believed to be non-toxic and non-allergic, making it especially suitable for injection or infusion administrations. Additionally, this levulinate formulation is reported as having a good taste, little irritation with a pH value of 7, and good stability such that no precipitation or deterioration occurs during use. Finally, this calcium levulinate formulation is also believed to have good compatibility with calcium lactate, calcium chloride, and other material complexes which allows the formulation to also complex effectively with a diverse variety of foodstuffs and pharmaceutical dosage forms.


5.2 MeSH Pharmacological Classification

Enzyme Inhibitors

Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)


5.3 ATC Code

A - Alimentary tract and metabolism

A12 - Mineral supplements

A12A - Calcium

A12AA - Calcium

A12AA30 - Calcium laevulate


5.4 Absorption, Distribution and Excretion

Absorption

General calcium absorption occurs primarily in the duodenum by an active transcellular and saturable system, which is stimulated and regulated by 1,25(OH)2D,25 and through a passive and vitamin D-independent paracellular transport in the jejunum and ileum, and even in the colon - where absorption is only about 4% even when the intake is high. Ultimately, calcium absorption depends mainly on the amount of intake - in general, absorption increases at lower intakes and decreases at high intakes. Readily accessible data regarding the specific absorption of calcium levulinate is not available although the formulation is considered a low molecular weight organic calcium ion type that is easily absorbed through the intestinal wall.


Route of Elimination

Calcium leaves the body mainly in urine and feces, but also in other body tissues and fluids, like sweat. Overall, a typical daily calcium loss for a healthy adult man or woman via renal excretion is approximately 5 mmol/day while endogenous fecal calcium losses are about 2.1 mg/kg per day in adults and about 1.4 mg/kg per day in children.


Volume of Distribution

99% of the body's calcium supply is stored in the bones and teeth where it supports their structure and function. Elsewhere, 1% or less of this calcium supply is used for essential metabolic functions like vascular contraction and vasodilation, muscle function, nerve transmission, intracellular signaling, and hormonal secretion, among other activities.


Clearance

Despite inter-individual differences, general clinical lab tests list some reference calcium clearance values as being considered a 'normal range', like urine calcium as approximately < 250 mg/24 h.


5.5 Metabolism/Metabolites

Although calcium levulinate dissociates into absorbable calcium ion once it is administered into the body, there have been studies to suggest that the levulinate component is metabolized to 4-hydroxypentanoate - a compound that has similar pharmacologic effects as but at a lower level of potency than the 'date rape' drug gamma-hydroxybutyrate.


5.6 Biological Half-Life

Readily accessible data regarding the half-life of calcium levulinate is not available.


5.7 Mechanism of Action

Much like most calcium supplements, once calcium levulinate dissociates in the body after administration, absorption of the supplemental calcium ions across the intestinal wall serves to enhance calcium stores in the body. Regardless, levulinic acid (LA) is a commonly used chemical with one carbonyl group, one carboxyl group, and alpha-H comprised in its inner structure, which belongs to short-chain and non-volatile fatty acids. Moreover, the carbon-oxygen double bond from LA's carbonyl group possesses a strong polarity, where the oxygen atom has a stronger electron attracting ability compared to the carbon atom, such that the pi electron will ultimately transfer into the greater electronegative oxygen, therefore resulting in the formation of a positive charge center in the carbon atom. The electrophilic center of the carbon atom subsequently plays a critical role when the carbonyl group performs chemical reactions. Owing to the relatively strong electron receptor effect of the oxygen atom of the carbonyl group, LA has higher dissociation constants than a common saturated acid, which allows it to possess a stronger corresponding acidity. Furthermore, LA can be isomerized into the enol-isomer, owing to the presence of the carbonyl group. The chemical structure of LA consequently has several highly active sites, which facilitates it being used as a chemical platform for preparing many other chemical products. For example, the special structure of LA allows various kinds of products to be generated by way of esterification, halogenation, hydrogenation, oxy-dehydrogenation, and/or condensation, among many other methods.


API Reference Price

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30-Jan-2021
28-Oct-2024
KGS
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Quantity (KGS) & Unit rate (USD/KGS) over time

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